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+1 for Gustto! I still carry my Baca and it is so soft...love itGustto is a brand that was talked about on TPF a lot a few years back. Their bags are very smooshy and unstructured. Not sure if you can still get new ones or if you'd have to look at preloved.
Look at Etsy- rough and tumble the 3 in 1 hobo. They are so awesome. Mine is very soft leather.
Yes. The Liebeskind. Also Linea Pelle. Really nice smooshy leathers.Are you in Europe? Both Liebeskind and Fredsbruder brands have lovely soft, squishy leather and an affordable price point. If you want delicious vintage-y leather, look at Campomaggi - a little more expensive, but really lush leather and maybe quite akin to your Scaramanga bag in style. The squishiest hobo I've ever owned was an Hugo Boss lambskin - it was huge and totally flaccid though (...ahem...) and I could never find anything in it, so I offed it. Ah, nostalgia...
- Lips <now humming theme tune to 'littlest hobo'>
Look at Etsy- rough and tumble the 3 in 1 hobo. They are so awesome. Mine is very soft leather.